This is a guest post by John Dooley who’s easily one of the most knowledgeable sports fans I have ever met. He’s a walking, talking encyclopedia of Cubs minutia, which explains his appearance on Comcast Sports Net’s ‘Batter’s Box’ trivia show. John’s true specialty, however, is crafting the lighter side of sports. See for yourself by visiting his blog Chicago Tough. Hilarious! @chicagotough

The Cubs are inching closer towards their first 100 loss season since 1966.

46 years.

That doesn’t seem right, does it? For most Cubs fans, it’s hard to believe that after all of the managerial flops, prospect flare-outs, and ill-fated trades that this magical number has evaded us for so long.

We all know that numerous teams (see: 1980, 1981, 1994, 1997, 1999, 2000, 2002, 2006, and 2010 Cubs) have had more than enough inept play to reach the mark. However, only this Cubs team has had the gumption to stick it to number 100!

If any hope exists for Cubs fans, maybe a comparison of the two teams could bring some light to a depressing season. There are some big similarities…

Both seasons were ‘culture shock’ years for the Cubs. In 1966, Wrigley had brought in Leo Durocher to bring in a winning attitude to the north side. Durocher was highly respected in baseball circles for his winning ways as a player in St. Louis, and in Brooklyn/New York as a manager.

In 2012, the Cubs’ move towards a ‘culture shock’ came through the hiring of Theo Epstein and Jed Hoyer. Both were forced to make tough moves on the field and off the field to bring a new attitude into the organization.

Under Durocher’s notorious tongue lashings, the Cubs limped through the ’66 schedule going 59-103. Durocher believed in ‘tough love’, and wasn’t one for sitting players for a day of rest. Durocher used 1966 as a training camp; a camp to find out who he could stand by in the years to come.

Durocher found out quickly that he had a team filled with potential. However, if the Cubs were ever to contend, some dead weight would have to go. It was obvious that Dick Ellsworth (who would lead the NL in losses) was past his prime. It was easily seen that Byron Browne (who led the NL in K’s) was never going to fulfill his duties in the outfield. It was also painfully obvious that the Cubs lacked depth on the bench, and even more severely in the bullpen.

Durocher’s Cubs had four future Hall of Fame players: Ernie Banks, Fergie Jenkins, Ron Santo, and Billy Williams (Well, five if you count the elder version of Robin Roberts in the pen). The foundation had been set prior to his arrival in ’66…but that didn’t stop the growing pains.

The Cubs were coming off the bizarre year of Bob Kennedy and Lou Klein. They were only years removed from the memorable gaffe that was the ‘College of Coaches’. Nobody in the Cubs organization knew anything about…well…organization. Durocher’s arrival would provide that organization…but at a price.

The Cubs would start 31-69 after 110 games…but as the players got used to Leo’s ways, they’d finish at a semi-respectable 38-44 to round out the season. Durocher had found ample arms in the rotation with Bill Hands and Ken Holtzman; plus, he made a big switch by moving Jenkins from the pen into the rotation. Talk about accomplishing a lot in one season.

For the 2012 Cubs, it’s hard to project four possible Hall of Fame players in this group. Nor can you compare the career accomplishments of Leo Durocher to Dale Sveum.

What you can compare is the level of change that was needed at both times in the franchise’s history.

The Cubs were a carnival act for the 1950’s and early 60’s and an over-priced act with little results during the 2000s, prior to Epstein’s arrival. 1966 and 2012 both stand as years to turn the tide.

While Durocher had to change the Cubs’ attitude in ’66, Epstein has had to change the Cubs’ way of doing business.

Epstein has started by being willing to deal players for prospects. In just one season, the Cubs have parted ways with Ryan Dempster, Paul Maholm, and Geo Soto. In return, they’ve upgraded for their future. He also finally laid down the law in refusing to negotiate contracts that feature the dreaded ‘no-trade clauses’.

However, in today’s baseball, the future you buy doesn’t come to fruition for another 2-3 years. Cubs fans in ’66 who were frustrated by the team’s consistent failure were quickly rewarded with a strong first half in 1967 that put the Cubs in first place by early July. While the Cubs faded down the stretch, it was obvious for many that the team would be a consistent contender for the next five years.

What Durocher was able to gain quickly, will take Theo & Co. much longer. As much as we might love Castro/Rizzo/Samardzija, it’s tough to compare them to Banks/Jenkins/Santo/Williams.

1966 had hope around the corner. 2012 has hope around the corner, too…just be prepared to also go left, through some trees, and maybe under a tunnel before reaching your destination.